Serratezomines D and E, new Lycopodium alkaloids from Lycopodium serratum var. serratum

Kubota, Takaaki; Yahata, Hiroko; Yamamoto, Sunao; Hayashi, Shigeki; Sato, Toshiro; Kobayashi, Jun’ichi

doi:10.1016/j.bmcl.2009.04.146

Cited by 23 publications

(12 citation statements)

References 10 publications

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“…Galanthamine was used as a positive control. Only species from the Huperziaceae family exhibited anticholinesterase activity ( H.nummularifolia (7)(8), H.carinata (9), H.squarrosa (10), H.pinifolia (11)(12)(13)(14)(15) and (B) Lycopodiaceae species; Lycopodium casuarinoides (16)(17)(18), L.clavatum (19)(20), L.platyrhizoma (21)(22), Lycopodiella cernua (23)(24)(25) inhibition…”

Section: Acetylcholinesterase Inhibition Assaymentioning

confidence: 99%

“…This is the first report on it's isolation from H. phlegmaria and acetylcholinesterase inhibition activity. Both the acetylcholinesterase inhibition values were within the range of bioactives isolated from the Lycopodiales order [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. The major limitation to this method is minor peaks below 10% area may have not been detected as it was not considered for the PLS analysis.…”

Section: Partial Least Squares Analysismentioning

confidence: 99%

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Biomarkers identification of Lycopodiaceae and Huperziaceae species from peninsular Malaysia with HPLC chromatographic profiling and partial least square analysis

Choo

Nor

Sahidan

et al. 2018

Separation Science Plus

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Crude herbal extracts are complex matrix consisting large quantity of plant metabolites. The identification of plant metabolite exhibiting bioactivity using the conventional bioactivity‐guided isolation process is a tedious and time‐consuming method. Club mosses from the Lycopodiceace and Huperziaceae families from Peninsular Malaysia is used as a model for this study since the alkaloid, (‐)‐huperzine A, exhibited acetylcholinesterase inhibition and used for the treatment of Alzheimer disease. The aim of this study is to evaluate the feasibility of using high‐performance liquid chromatographic profile and applying partial least square projection to identify the biomarkers. A high‐performance liquid chromatography gradient system with increasing amount of acetonitrile in deionized water and an ODS‐3 column (250 × 4.6 mm) was developed for the acquisition of the chromatographic profiles. A colorimetric assay was used to analyze the acetylcholinesterase inhibition activity. Both the pretreated high‐performance liquid chromatography integration data and acetylcholinesterase inhibition results were subjected to chemometric data analysis. From the unsupervised principal component analysis results, no outliers were detected and the data was further subjected to partial least square projections. Two biomarkers were identified and were isolated and structurally elucidated as 6β‐hydroxyhuperzine A and (‐)‐huperzine A.

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Section: Acetylcholinesterase Inhibition Assaymentioning

confidence: 99%

Section: Partial Least Squares Analysismentioning

confidence: 99%

Biomarkers identification of Lycopodiaceae and Huperziaceae species from peninsular Malaysia with HPLC chromatographic profiling and partial least square analysis

Choo

Nor

Sahidan

et al. 2018

Separation Science Plus

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“…A previous investigation revealed the presence of the five alkaloids, huperzines A and B, lycodoline, lucidioline, and lycopodine (TLC evidence), but there is no report on the isolation of pure compounds [9]. As a part of our research on structurally unique and biologically active compounds from medicinal plants of Yunnan, China, we have isolated and identified a new alkaloid, 15a-methyllycopodane-5b,6b-diol N-oxide (1), as well as the two known alkaloids, 15a-methyllycopodane-5b,6b-diol (2) and lycoposerramine H (3), and the four serratene-type triterpenoids, serratenediol-3-acetate (4), serratenediol (5), lycocryptol (6), and serratriol (7) from P. yunnanensis [10 -14]. This article focuses on the isolation and structural elucidation of compound 1.…”

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confidence: 99%

“…A new lycopodine alkaloid, 15a-methyllycopodane-5b,6b-diol N-oxide (1), was isolated from the whole plants of Phlegmariurus yunnanensis Ching, together with the two known alkaloids 15a-methyllycopodane-5b,6b-diol (2) and lycoposerramine H (3), and four serratene-type triterpenoids, serratenediol-3-acetate (4), serratenediol (5), lycocryptol (6), and serratriol (7). Their structures were elucidated on the basis of spectroscopic analyses, including HR-ESI-MS, 1 H-and Introduction.…”

mentioning

confidence: 99%

A New Lycopodine Alkaloid from Phlegmariurus yunnanensisChing

Xie

Jiang

Liu

et al. 2010

Helvetica Chimica Acta

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A new lycopodine alkaloid, 15a-methyllycopodane-5b,6b-diol N-oxide (1), was isolated from the whole plants of Phlegmariurus yunnanensis Ching, together with the two known alkaloids 15a-methyllycopodane-5b,6b-diol (2) and lycoposerramine H (3), and four serratene-type triterpenoids, serratenediol-3-acetate (4), serratenediol (5), lycocryptol (6), and serratriol (7). Their structures were elucidated on the basis of spectroscopic analyses, including HR-ESI-MS,

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“…The CHCl 3 fraction yielded the known huperzines A and B (3 and 4, resp. ), phlegmariurine (6), and (8b)-8-hydroxyphlegmariurine B (7) after repeated chromatography.…”

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confidence: 99%

Two New Lycopodine Alkaloids from Huperzia serrata

Jiang

Liu

Min³

et al. 2010

Helvetica Chimica Acta

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Two new lycopodine alkaloids, (12b)-12-hydroxyhuperzine G (1) and (5b,6b,15a)-15-methyllycopodane-5,6-diol (2), were isolated from the whole plants of Huperzia serrata, together with six known compounds, huperzines A, B, and G, phlegmariurine B, (8b) Introduction. -Huperzia serrata (Thunb. ex Murray) Trev. (Huperziaceae) is one of the most commonly used traditional Chinese herbal medicines for the treatment of contusion, strain, swelling, and schizophrenia [1]. Previous investigations have shown that it contains many alkaloids with novel and diverse structures including huperzine A, which was reported to increase efficiency for learning and memory in animals and show promise in the treatment of Alzheimers disease and myasthenia gravis [2 -5]. Further, numerous efforts on the isolation of new potent alkaloids from H. serrata and other related plants have been carried out by many research groups [6 -8]. Up to date, most of the isolated alkaloids are liposoluble. As a part of our research of structurally unique and biologically active compounds from medicinal plants of Yunnan, China, we isolated and identified two new alkaloids, (12b)-12-hydroxyhuperzine G (1) which is hydrosoluble and (5b,6b,15a)-15-methyllycopodane-5,6-diol (2), as well as six known compounds, i.e., huperzines A, B, and G (3 -5) [2] [9] [10], phlegmariurine B (6) [11], (8b)-8-hydroxyphlegmariurine B (7) [12], and lycoposerramine D (8) [13], from H. serrata. This article focuses on the isolation and structural elucidation of 1 and 2.

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Serratezomines D and E, new Lycopodium alkaloids from Lycopodium serratum var. serratum

Cited by 23 publications

References 10 publications

Biomarkers identification of Lycopodiaceae and Huperziaceae species from peninsular Malaysia with HPLC chromatographic profiling and partial least square analysis

Biomarkers identification of Lycopodiaceae and Huperziaceae species from peninsular Malaysia with HPLC chromatographic profiling and partial least square analysis

A New Lycopodine Alkaloid from Phlegmariurus yunnanensisChing

Two New Lycopodine Alkaloids from Huperzia serrata

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